


Gabriel

by bmlhillenkeene



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Crossdressing, Genderfluid!Gabriel, M/M
Language: English
Status: In-Progress
Published: 2014-08-18
Updated: 2014-08-20
Packaged: 2018-02-13 17:38:29
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 10,269
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2159310
Author URL: https://archiveofourown.org/users/bmlhillenkeene/pseuds/bmlhillenkeene
Summary: <blockquote class="userstuff">
              <p>Sam is having a hard time coping after the death of his longtime girlfriend Jessica. To the point where ever looking at another girl feels like a betrayal. Until he meets Gabriel.</p>
            </blockquote>





	1. First Meeting

**Author's Note:**

> So this has been sitting in a notebook with the first 4 chapters written for ages and I have yet to post it. Nows the time.
> 
> Forgive me my madness.

All my life there had been five people I had ever felt comfortable calling family, and of those five, only two were family by blood.

My mother died when I was six months old, leaving my father and older brother my only living family. My father was a big man, tall and burly. He worked as a labourer on building sites, I remember, growing up, hating that he was always away so much, always working. I resented that I hardly got to see him, and when I did he never wanted to play. I know now it was because he was tired, that he’d thrown himself into his work with even great fervour than ever before because if he didn’t, my mother’s death might have broken him completely.

As it was, his absence left me in the company, most often, of our neighbour Missouri Mosley, she’d come over from Africa as a refugee sometime in her twenties, married a nice young white man in a time when it still wasn’t considered ‘proper’ to do so, raised a bushel of kids, all of whom visited her tiny little flat every Sunday with their own children in tow to have dinner. She was an imposing woman for someone so frail looking. She’d been nearly sixty when she’d started looking after me and my brother, and we could never get anything past her.

Which leads me on to my brother, Dean, who has, and always will, probably been both the biggest influence and pain in my neck in my life. He ran wild after our mother died, at the age of seven he became one of the biggest trouble makers in our street and Dad was constantly getting neighbours complaining about him. He’d hated everything for such a long time, even me, until he’d met the fourth member of my little family.

James Castiel arrived at Dean’s (and later my own) primary school three years after mom had died. Dean had been classed as the school bully by then, and had thought nothing of picking on the skinny new kid with the funny name. Right up until Cas had punched him in the face. The two became fast friends during the break time they were forced to sit out as punishment and have been inseparable ever since. Cas was over at ours so often that Dad joked he’d had another son when he wasn’t looking. But Cas helped keep Dean from straying too far down the wrong path, and was always there for me if I needed him.

The last member of my little family was Jessica. I’d met her in high school, and she was the most beautiful girl there. It took me three years to work up the courage to ask her out (much to my brothers, consummate ladies man that he is, amusement). When she agreed I was the happiest guy in the world. We were inseparable, always together. Regular date nights, holding hands, walking each other to class, the whole thing, up to and including spending the night at each other’s houses, when we were old enough, with the blessings of our parents.

Then I’d gotten accepted into college, a good one, miles away from home. She was staying in our home town, going into training to be a hairdresser; she wanted to open her own salon and was pursuing it with a single minded determination. I loved that about her, that determination. But she, and everyone else, encouraged me to go and I did. She was dead before I’d even finished my second term. A car accident, the car she’d been in hit a patch of black ice on the road and just like that she was gone and all our plans to get married have kids, get her salon up and running, was gone with her.

I nearly didn’t go back to University after that. Was prepared to wallow in my grief for years to come. Dad, Dean, Missouri and Cas bullied me back, determined not to let me grieve forever. I hated them for it, for a long time, before I got back into the routine of University life. But I was different now, and there was no changing that.

Since then I didn’t look at girls with any real interest, just a passing glance before something about them would remind me of Jess and I had to turn away. In the spirit of experimentation, I’d turned my attention to men. I hadn’t migrated across the fence completely; it was just easier sometimes to fall into bed with another guy. No attachments or commitments, just a willing body that didn’t stir up memories of Jess.

All that changed though, when she slammed into me in one of the corridors on the way to class. I’m as tall as my Dad, even if I’m not as built, and she didn’t do much more than rock me back a step. She however, did an impressive, arm flailing, stumble before I managed to catch her and set her back to her feet.

“Sorry.” I said, reflexively, even it hadn’t been my fault. I had gotten into the habit of apologising when I was a kid, being so much taller than everyone else made me awfully clumsy, and I’ve never really grown out of it.

“No problem.” She replied. Her voice was deeper than I was expecting, but it was nice. She straightened up from fixing her skirt, a knee length flared denim thing I had never seen Jess, or any other girl wear. It clashed horribly with the converse boots and the yellow and black striped tights, bright yellow t-shirt and a denim jacket in a completely different shade of blue. She looked like she’d dressed in the dark, a far cry from any other girl I had ever met who were all so meticulous in how they looked.

“Wow! You’re tall.”

Her voice cut through my musing, making me realise I’d been staring at her, comparing her relatively flat chest (which was broader than I’d expected) to the memories of Jessica’s slimmer, fuller figure. I blushed guiltily and refocused my attention onto her face.

I was met with a knowing smirk.

She wasn’t pretty, not in any way I could quantify; her features were boyish, even with the makeup softening the hard lines. Her eyes were a captivating shade of Honey, sharp and intelligent.

“So, my names Gabrielle.” She drawled out, rolling the end of her name neatly off her tongue, her accent indeterminate, but it definitely had a foreign twang to it, French maybe? “I think you ought to move out of my way so I can get to class. Sasquatch.” Her tone was amused as she watched me.

I suddenly realised I was blocking her way, though she could just have easily walked around me if she’d wanted to. I stepped aside. “Sorry.”

She took a step forward and smiled up at me. “You’re cute. What’s your name?” she asked.

“Sam.” I answered, surprised.

She nodded and shot me a cheeky grin. “See ya around Sam.”

And then she took off like a barely contained ball of mismatched colour and energy and I spent a long moment staring after her before shaking my head and continuing on to my own class.


	2. Second Meeting

I didn’t see Gabrielle again for another two weeks. Though I often found myself searching all the communal areas of the University for a Mismatch of ridiculous colour. I even found myself standing in the corridor where I first met her, loitering around. I gave up after a week with no luck. The constant snark from my dorm mates didn’t help any either. I regretted letting them get me drunk enough to tell them about my encounter with her. 

Besides, they may have had a point, trying to find someone using bad fashion sense as a guide was hardly the most sensible thing to do. It had probably been laundry day when I met her. God knows I’d had to wear some bizarre combinations of clothes until I’d managed to wrestle my washing down to the machines sometimes.

The fact that I was still thinking about her after I’d all but given up on seeing her again, surprised me. She was about as far from Jess as I’d even seen a girl be; which made sense, in some kind of a twisted way. But still, the attraction surprised me, nothing about her put me off like other girls usually did.

I’d managed to restrain myself from calling my brother and telling him about this mystery girl when we’d talked on Sunday. The teasing he would have given me for trying to find her again like I had I could handle. It would be the celebration of my renewed interest in women that I wouldn’t be able to cope with. He had been harping on at me to at least try dating again for over a year. I was surprised he’d lasted so long before trying to get me back on the horse, so to speak, but I guessed I probably had Cas to thank for that.

I hadn’t told Dean or my Dad about my sleeping with guys, not that I thought they’d have a problem with it, but I knew they’d point it out for what it was, a way to avoid a repeat of Jess, and though I could admit it to myself, I didn’t want to hear it out loud.

When my dorm mates suggested I join them at the students union for a Friday night of clubbing and drink, I agreed, just for something to do, and to keep them off my back about never having any fun. It was not, I told myself firmly while picking out my best shirt, to try and find the mystery girl again.

~*~

The hall was large and noisy and filled to bursting. The music pounded some heavy dance beat, loud and relentless. I’d somehow ended up on the far side of the room to the bar, and had been abandoned by my dorm mates pretty quick when they’d disappeared into the dancing mass that stood between me and another beer.  
I’d been nursing my second beer for nearly half an hour, trying to make it last so I wouldn’t have to brave the heaving, sweaty mass of grabby hands and pure un-coordination that made up a good portion of the dance floor at this point with how drunk everyone was getting, when I heard her, or at least, I thought I did.

“Samsquash!”

I nearly dropped my beer as I tried to catch her, stopping her from cracking her head against the wall I was leaning on. She looked up at me with a beaming grin, face flushed and her eyes a little glazed from all the dancing, and the drink. She was dressed in the most hideous pink glittered dress I’d ever seen, complete with pink glittery high heels and an obscene amount of body glitter glistening on her skin. She shouldn’t have looked good, but somehow, against all odds, she did.

She wobbled on her heels when I let her go and leaned into my side to steady herself. Even in heels she was at least half a foot shorter than me.

I searched for something to say, before I remembered her greeting. “Samsquash?” I asked her, leaning down towards her so I didn’t have to shout so loudly.

She grinned at me. “Took me ages to think that up.” She said. “Suits you though.” And she reached up to ruffle my admittedly shaggy hair, before looping the hand at the back of my neck to pull me closer. “I need some air. Wanna join me?”

I blinked, sure I was mishearing the suggestion in that invitation, but I was met by an easy, suggestive smirk and she turned away, bracing herself on the wall as she wobbled again on her heels before she found her balance and walked away. I watched her go, debating the wisdom of following her. Was this going to be a one night stand, or something more? 

Did I want it to be something more?

My feet were already moving before I’d even considered it. I’d spent two weeks thinking about her, and at least some part of me wasn’t about to let her disappear on me again. She was sitting on one of the picnic tables set up outside the building for those warm afternoon drinking sessions, wrapped up in a shrug, a pink glittered bag on the bench beside the table, her legs swinging.

She was practically sparkling in the faint lights of the street lamps and I found myself grinning as I made my way across to her. “Wearing enough glitter?” I asked, teasing.

She gave me a scowl, but it broke into a cheeky grin too quickly to be taken seriously. She ignored my questioned though, waiting until I came to stand between her legs, before reaching up and tugging me down. “You are too tall.” She told me very seriously.

I ducked my head down closer to her and smiled. “I think maybe you’re just too short.”

There was a sudden flash of uncertainty that crossed her face, but it was gone too fast to be absolutely certain I wasn’t imagining it. The fact that she dragged me into a kiss didn’t help me focus on it much. It was hard and fast, an awkward clash of teeth and lips.

She pulled back, but I didn’t give her the chance to go far, following and reclaiming her lips as quickly as I could. We kissed until my lungs burned and we were forced to pull away, both of us breathless and flushed. She was clutching at my shirt, breathing hard and looking at me like maybe it was the best kiss she’d ever had… and maybe I wasn’t going to disagree to that assessment.

“I think.” She panted a little, tugging me down for another kiss before continuing. “I think we ought to take this back to your room. Unless you have an exhibitionist kink you’d like to share.”

I nodded. “Yeah.”

It wasn’t until she started laughing that I replayed what she said and felt my face heat up. “I meant- I don’t have a… Oh God!” it was humiliating.

Her hand tightened on my shirt, not letting me detangle myself from her. “I know.” She smiled. “It was a joke.”

I nearly missed the second flash of uncertainty that flitted across her face. “Hey. We don’t have to do this you know. If you don’t want to.” I offered. Maybe she thought she had to offer to have sex with me. Maybe that was how it was done? It wasn’t like I really knew; I’d only been with Emma before, and all the guys I hooked up with were more than happy to tumble in the sheets with me. I was more than happy with just the kissing if that was all she wanted to do.

She bit her lip and glanced aside. “No. I want to.” She said. I might have believed her if she didn’t look so nervous. “It’s just that…” she chewed at her lip and finally looked back at me, considering. “Oh fuck it!” she muttered to herself. “I’m a guy, biologically speaking.”

There was a pause, a long moment of silence where I tried to get my head around that statement. My eyes darting all over her face, searching for the proof, or a way to deny it. I wasn’t sure which one I would have preferred.

“Please tell me this isn’t going to send you running screaming?” she-he?- asked, shifting back on the table, putting a little space between us.

It was probably the longest, most awkward moment of my entire life. My mind racing in a confusing jumble of thoughts that I couldn’t make head nor tails of. But then I saw the uncertainty on her-his?- face shift to something that could so easily bloom into fear, and I couldn’t stop myself leaning forward and down again and kissed her-him.

“So. Do I call you Gabrielle or Gabriel?” I asked when I pulled back.

I was met with a, pleased, near blinding smile. “Gabriel. You can call me Gabriel.”


	3. Spending the Night

It didn’t take long to get back to my dorm room. Normally I didn’t take anyone back there, but Gabriel told me he didn’t live on campus. So my room it was. It took even less time to get there after I scooped Gabriel up into my arms the second time he stumbled in his heels, earning a squawk of surprise and a faux southern belle “Ma hero!” for my trouble.

When we got there we just sort of fell into my bed, still untidy from where I’d gotten out of it this morning. There was nothing sexy, or evocative, in the hasty, curse filled attempts to rid ourselves of our clothes as quickly as humanely possible so we could get to the good part.

When he’d finally wriggled out of the glitter dress and heels, Gabriel gave me the biggest, hungry looking grin, and I was surprised to find myself on my back on the bed. It was easy, in a way I hadn’t really expected, but once he was out of the dress Gabriel was just like any other guy I’d been with. Though I did get the added, guilty thrill, of removing the silky bra and panties he had left on.

It had been one of my favourite things about sex with Jess, but for once I wasn’t thinking about her, my whole attention was focused on Gabriel, and the way his skin felt under my fingers as I slid the straps of the bra off his shoulders as he perched on top of me, smiling indulgently, like he knew it was my kink.

The rest of the night disappeared in a haze of fumbling for condoms, rubbing and touching. Kissing and nipping at sweat soaked skin, until I came hard, and watched Gabriel shiver his way quietly through his own mere minutes later under my teasing hand.

There was the clean up after of course. But when Gabriel made vague noises about leaving, I found I couldn’t let him, and he didn’t put up much of a fight when I manoeuvred him back into the bed and curled up behind him, sliding an arm around his waist to keep him from falling off my tiny little single bed.

~*~

It wasn’t so much the ringing of a phone that woke me the next morning as the feeling of Gabriel trying to wriggle out from under my arm. I half opened my eyes when he finally managed to escape my grasp and watched him search for his bag and root around inside it until he pulled out a plain black phone. Rubbing his eyes in a way that should not look as adorable as it did on a half-naked man still covered in body glitter, Gabriel answered the phone.

“Hey.” He said, and then listened for a moment, rooting amongst the pile of clothes for the underwear I had unceremoniously tossed aside last night, tugging them on one handed while he answered. “Yeah, yeah, yeah. I spent the night with someone.”

Gabriel’s eyes canted over to me. I debated pretending to still be asleep, to give him some semblance of privacy while he talked, but he caught my eye before I could make the decision, and he smiled at me, completely unbothered.

“No I will not tell you who.” He rolled his eyes at me in that way that said all too clearly Family. So either a parent or a sibling I supposed. “Yeah I’m going to need a change of clothes.” He continued. “No, I don’t think they’d be impressed with me showing up in my glitter dress.” He lifted said dress as he spoke, looking it over critically, before suddenly flushing in embarrassment. “Uncle Crowley!” he hissed out. “Ok. I’ll meet you at the gate in ten minutes.” He closed his eyes for a moment as if praying for strength. “Yeah, I’ll be there.”

He hung up with a sigh. “Sorry, my uncle worries.”

I pushed back the quilt and swung my legs out, groping beside the bed for my boxers. “Want me to walk you to the gate?” I asked

Gabriel gave me a pleased grin before shimmying back into the glitter dress, which looked even more hideous this morning. “Nah, it’s ok. Unless you have a burning desire to meet my over protective uncle. In which case, sure, no problem.”

I considered it briefly before shaking my head. “Don’t think that would be a good idea.” I managed to bite back the “Yet.” That tried to slip through, surprising myself. If Gabriel had really been a girl, would I have insisted to walk him across campus to the main gate? I didn’t know, and that bothered me a little.

“No problem.” he said easily. He didn’t seem insulted in the least, which made me feel a little better. Finally dressed he gathered up his heels and padded across to the door, pausing with a small, uncertain smile. “We should do this again.”

If it hadn’t been for the smile, I might have thought he was being cocky. I found myself nodding with a smile. “I’d like that.” I got a repeat of that beaming smiled from the previous night before Gabriel unlocked the door and slipped out.

I flopped back on the bed. I wasn’t exactly sure what was going on here. But I didn’t bother fighting back the sudden smile that settled comfortably on my face.


	4. Third Meeting

I regretted not getting Gabriel’s number before he’d left that morning. I spent the next week on the lookout for him. My dorm mates were still teasing me about how I was still searching for my mystery girl, I let them tease. Most of the week I spent thinking, in between classes, about him, trying to decipher him, as if that could somehow help me work out just why I seemed to be falling so hard for him.

Did I like Gabriel because he was a man, or because he dressed like a woman? I figured it to be a legitimate question. Was I interested because he was as close as I was going to get to being with a woman? Or was it because I liked him. Taking into account that I had thought he was a she before that night, it was more likely to be the latter.

But I had never identified as being gay, never. All the guys I’d been with, they were just convenient. Though, to be fair, I’d never really been interested in any other girl but Jess, she had always been it for me.

Until now.

That scared me. How quickly I’d found myself falling. How easy it was to think about Gabriel and to have my brain leap to six months from now, a year, five, and all the things we would do together in that time. 

I was in the campus cafeteria; I had my lecture notes spread out in front of me, doing my best to keep my mind off Gabriel for a while. Which had been working about as well as I had expected it to, which was to say, not at all.

“Hey Sam.”

I startled, only just managing to save a stack of notes from ending up all over the floor. “Gabriel?” I looked up, surprised, though I suppose I really shouldn’t have been. Gabriel had an odd habit of showing up just when I thought I might not see him again.

“The one and only!” He chirped cheerfully, settling himself on the seat across from me, carefully setting a travel mug down on a clear bit of table. He was dressed very differently to the other times I had seen him, wearing a ripped pair of jeans and a tie died t-shirt. If it wasn’t for the multi-coloured nail varnish and the faint sheen of lip gloss he would have looked positively normal.

A part of me was glad he didn’t.

“Uh-hey.” Was my brilliant rejoinder to the conversation and I felt myself flush. What was it about him that made me flustered so easily?

Gabriel grinned. “You are cute.” He told me shamelessly. “Though if you don’t tone it down a little, my ego might fill the whole room.” He settled himself more comfortably in his chair and looked at me intently. “So, I’m betting you have questions.”

I opened my mouth to answer, only to realise I didn’t even know what I wanted to say. What sort of questions could I ask? Where was the line drawn between curiosity and insult?

Gabriel laughed. “I’ll start then shall I?” he asked teasingly, lifting the travel mug and opening the little tab on top to take a drink. Hot chocolate, which seemed fitting somehow, with what little I knew about him. “Question: ‘Gabriel, why do you wear women’s clothes?’ Answer: ‘Because I want to.’ Question: ‘Why are you not wearing a pretty skirt today?’ Answer: ‘Because I didn’t feel like it.’ Question: ‘Is sex with you always that good?’ Answer: ‘Do you want to find out?’” 

He wiggled his eyebrows at me, and just like that the ice was completely broken and I laughed. “You are weird!” I chuckled, reaching to tidy up my books and notes to make more room on the table.

Gabriel grinned and settled his arms on the newly cleared space. “I’ve been called worse. Where have you been hiding yourself?”

“You’ve been looking for me?” I asked in surprise, not that I should have been I suppose, but it was sort of nice to hear that I wasn’t the only one getting invested.

He shrugged easily. “Yeah. Forgot to get your number.” He said. “Might have remembered if my Uncle hadn’t been harping at me to get home.”

Curiosity got the better of me. “You live with your Uncle then?”

“Uncles, well, cousins. Balthazar is my second cousin by blood. Uncle Crowley is his ‘Life Partner’, which basically means he’s his life manager. Balthazar would be completely useless without him.” Gabriel grinned, taking another drink from his travel mug, making a small, blissed out sound that made me shift a little in my seat. “You didn’t answer my question though.” He continued, smirking a little like he knew just what that sound had done to me. “Where have you been hiding?”

I shrugged. “I haven’t been hiding.” I told him, and then ploughed on, unable to stop myself from teasing him a little. “Though it would have been hard for you to see me, what with everyone being so much bigger than you.”

Gabriel snorted a laugh before schooling his expression in an annoyed frown. “I see how it is. Making fun of my size huh? I’ll have you know I am perfectly sized. You’re the one who’s freakishly tall. I mean seriously, you’re a giant!”

I had always been particularly self-conscious about my size, my Dad and I had always towered over everyone else we knew, but without his bulk, which my brother had inherited, I ended up seeming taller than I really was. But it didn’t feel like it had when Gabriel said the exact same things the bullies of my youth had.

We fell into comfortable conversation, like we’d been friends for months, if not years. I found myself telling him about my Dad and my brother, about Missouri and Castiel and life back home. About the fact the Mom was dead. I didn’t mention Jess; she was too fresh still, even after two years. 

Gabriel rallied back with stories about his uncles, and if he didn’t mention anything about his parents, or his life before he turned seventeen, I wasn’t going to pry. He did explain the cross dressing though. “It’s not,” he said, picking at the table edge with a finger nail, “that I want to be a woman. I’m pretty happy being a guy most of the time. I’m pretty happy being gay. I just like the clothes, and the shoes, and the makeup.” He smiled a little, shrugging. “Women just have so much more choice, and I find it… I don’t know. Comfortable I guess.”

And that was that.

We flitted through other topics, like how he was doing Drama and English Lit, watched everything and anything providing there was at least one good looking guy in them (though he admitted a newfound fondness in the old show Smallville, and then smirked at me until I made the connection between the tall, shaggy haired main character and myself). He devoured anything sci-fi, or to do with the apocalypse. And apparently would try and subsist on chocolate if his Uncle Crowley hadn’t put his foot down on at least one normal meal a day.

He was, in almost every way, the complete opposite to me. I was doing law as my degree, tended to watch documentaries and historical dramas over anything else (though the odd Bruce Willis film was always a temptation). But my passion was mainly history and myths. But for some reason, it didn’t bother me that we were so different.

Finally the conversation wound down and we sat in silence.

Gabriel broke it, hands messing about with the long empty travel mug. “So, I like you.” He said seriously, not looking at me. “But I heard you don’t sleep with guys more than once.” He didn’t give me a chance to answer before ploughing on.

“And I know the whole cross dressing thing is pretty off putting for a lot of people.” His eyes skittered around the room for a moment for he looked at me. “But I like you. And I’d like to go out with you.”

“Okay.”

It took me a second to realise I’d said that, immediate and absolutely no hesitation or second guessing. The word had just ripped out of me before Gabriel had even finished speaking. I ploughed on, because I couldn’t backpedal out of it, and I really didn’t want to. “Yes I would like to go out with you please.”

Gabriel looked like I’d struck him completely speechless. Like he hadn’t actually expected the response he’d gotten. He stared at me wide eyed and opened his mouth like he intended to say something, but just couldn’t get the words out.

I was thrown back to when I was fourteen and asking Jess out for the first time. Waiting for something to break the awkward silence, to break through the growing embarrassment. And then Gabriel’s face cracked into another beaming smile, wide and pleased. I decided right then that I couldn’t quite get enough of those smiles.

And that, as they say, is that.


	5. First Date

My first date with Gabriel was nerve wracking, for a number of reasons. It had been so long since I had dated anyone. Far too long, and all the things I considered to be normal date seemed juvenile. Gabriel had teased me nonstop since I’d texted him to ask for a proper date, which hadn’t helped. Eventually I’d decided on dinner and a movie, and Gabriel promised to meet me at the local cinema.

I arrived early, hanging round nervously, wondering what the proper way to greet him when he arrived would be. Would he be coming dressed as a man or as a woman, and did that make a difference? Should it? A date shouldn’t be that hard, not after I’d already slept with the guy. But it was.

I hardly recognised him when he did show up; he was dressed in men’s clothes, dark jeans, and faded Loki t-shirt under a leather jacket that looked like it had seen better days. These were comfortable clothes, like a layer of protection. His nails were an iridescent green, and though he wasn’t wearing makeup on his face, one side of his hair was clipped up with green glitter clips, like the one’s little girls wore to school.

The sight of these made me feel better, where the clothes had made me worry. There was more to the way Gabriel dressed than I understood, and I could acknowledge that, but so far I had only ever seen him in women’s clothes, even the jeans he had worn before had been women’s. This was my first time seeing him look really masculine.

It was the first time I realised that he might be actually nervous, despite his teasing.

“Hey.” He greeted, glancing round.

“Hey.” I said, wiping my palms against my jeans, debating what to do. This was a fairly accepting sort of place, but still, I still wasn’t sure of the proper way to greet him.

There was a horribly awkward moment where neither of us did anything, and the Gabriel rolled his eyes and stepped forward. “Don’t freak out.” He said sternly, with just a hint of teasing, and tugged me down.

“Oh good.” I found myself saying when our lips parted, glad I now knew what was ok, and leaned in to kiss him again.

He grinned when we parted again. “Food Samsquash.” He reminded me.

I brushed my fingers over the slightly rough glitter on the clips. “Ok then.”

The rest of the date went off without a hitch, thankfully, though there were more than a few false starts, while I felt my way around an act that had been as natural as breathing with Jessica. Did we hold hands? Did men do that with other men? Was it ok with Gabriel anyway? Should I react if someone made a comment they shouldn’t? Or should Ii leave it to Gabriel?

It wasn’t something one date was going to tell me, but for the most part I deferred to Gabriel.

We ended up at mine again after, fumbling around in the dark because neither of us thought to hit the light switch. It was different without drink in the way, and I think that it was then that sort of cemented for me that Ii really was interested in Gabriel, because tugging his boxers off him was no less guiltily fulfilling as doing the same thing to the panties he had been wearing the first time.

As with the last time neither of us pushed further than rubbing, kissing and mutual hand jobs, but it felt somehow more intimate this time. It felt like I was maybe seeing Gabriel as he wanted to be seen, an odd mix of two genders, not really one or the other.

Though that may have been my imagination.

One thing I did realise, much later, when I woke up well before dawn, my arm tight around Gabriel’s waist, was that I needed to tell my family.


	6. Telling the Family

It took me another two weeks before I finally worked up the courage to drop. “So… I’m seeing someone… here, in college.” Into my Sunday afternoon call to my brother.

The silence that followed that bombshell was nothing short of shocked, and eventually I could hear Dean spluttering back into the conversation with, “You mean like dating Sammy?” like he had to be absolutely clear that Ii was actually dating someone, and hopefully having sex with them, because that was what Dean was like.

“Yeah Dean, like dating.” I rolled my eyes.

“Huh.” Was the oh so eloquent response to that, and I knew I really had surprised him, that he hadn’t actually thought he’d hear me saying those words ever again. Dean knew it had to be serious, because he knew me. He knew me so well it hurt sometimes.

“Yeah.” I answered him.

“She cute?” Dean asked.

I had debated how much I should tell Dean, because the first thing he was going to do was tell Dad, followed very swiftly by Cas. I knew none of them had any problems with homosexuality, after all, there had been a long time when we were all sure that Dean and Cas were going to end up together, and while their attempt at a relationship hadn’t worked out, it was still looked back at fondly by the two of them, and they had come out of it as stronger friends.

Dean had since moved on to dating Cassie, Missouri’s granddaughter, and Castiel had met Amelia in college, the only person in the world he would ever let call him Jimmy, if what Dean told me was true.

So no, I wasn’t worried about how they would take it if I admitted to liking a guy. But my dad, and Dean to a lesser extent, did have old fashioned notions of what men and women should be like, and men should not try to be women and women should not try to be men. So Gabriel would be a huge shock to them, one I wasn’t sure I wanted to expose them too just yet.

“He is.” I said at last. “Or at least I think so.”

There was silence again, and I waited for Dean to process that. “Sammy.” He said then, and his voice was softer than it should have been, and I didn’t think I could take it if he started talking about Jess, so I jumped it.

“It’s not like that!” I said, clenching my teeth, because it wasn’t, Gabriel was so far from Jess that it was completely impossible to compare the two, and I didn’t even have to make myself not do it, so if that didn’t just say it all I didn’t know what else would. “Gabriel is… He’s different Dean, in a really, really good way.”

“Ok.” Dean said at last. “Ok, Sammy, if you’re sure.”

“I am.”

“Ok then. So long as you like him, and you’re sure, then that’s fine, good, better than good.”

I frowned a little at the odd tone in his voice. “Are you freaking out?” I asked him.

“No!” he snapped, and I couldn’t help laughing, because he totally was. He spluttered a bit down the phone before growling noisily. “Shut up, Bitch.”

“Jerk.” I snickered.

“Want me to tell Dad?” he offered.

“If you could warn him that would be good.” I said, because it was normally a very good idea to have Dean pre-warn Dad of any issues before I spoke to him, because despite both of our best intentions, we would end up screaming at each other if one of us was caught unawares. I did feel sorry putting Dean in the middle, but I knew he’d make sure Cas was there before saying anything. Cas was a very good mediator in the Winchester family problems, and if the worst came to the worst, one of them would pull Missouri in to talk to Dad.

We wrapped up soon after, and Ii debated calling Gabriel before deciding against it, shooting a text off instead. He phoned back less than 30 seconds later.

“Are you ok?” I was surprised by the real worry in his voice. I could hear the sounds of the TV in the background and two men talking quietly.

“I’m fine.” I said, confused, nothing in my text should have brought out this level of concern.

“You swear?” he pressed. 

“I swear.” I answered promptly, wondering at the sigh of relief. It only hit me after that, the gaps in conversation where Gabriel’s life before 17 should be, that maybe his own coming out, be it as gay, or that he liked dressing in girls clothes, had not gone so well. “My brother dated his best friend Castiel for a while at the end of high school; we’re not complete strangers to alternative lifestyle choices.” I reassured.

Gabriel made a small noise, but I took it as a good sound. “I’ll be talking with my dad later about it.” Though I wasn’t sure if it would be tonight or tomorrow.

“Your dad?” Gabriel said, and there was a tense note to his voice that I didn’t like. “Will he be ok with it?”

“He’ll be fine with it, once he gets over the shock of me dating again.” I said, grimacing when I realised what I said. I hadn’t yet told Gabriel about Jess, or why I hadn’t dated anyone before him. He ignored the opening to ask, and Ii was grateful that he seemed too worried to really notice. I’d get around to telling him about Jess, at some point before we got really serious.

“You’re sure everything is ok? Will be ok?” Gabriel pressed.

“I’m sure.” I promised, wishing he was there so I could pull him into a hug, it sounded like he needed one.

“Ok.” Gabriel took a deep breath. “Call me after ok? No matter what.”

I smiled, because it was sort of cute. “I will, promise.”

There was some awkward fumbling, and I imagined Gabriel was probably a little embarrassed he’d overreacted. But if I was right about why, then it was understandable. I set my phone on charge and waited for my Dad to call, pulling out some study notes to stop myself from getting a little nervous myself, because I wouldn’t be able to derail Dad from bringing up Jessica, and I needed to make sure I didn’t blow up at him for it.

The call came at half nine that night, and was a great deal longer and lacking in any of our usual banter. Neither of us ended up shouting, which could only be a good thing, and Dad made me promise to bring him home for part of the summer if we were still going out by then.

I got a text from Cas much later, delayed by my promised call to Gabriel, to say Congratulations.

Now I had until the Summer, because I was sure Gabriel and I would still be going out then, to prepare my family for him.


	7. The Invitation

It was easier than I ever thought it could be to fall back into the routine of dating. Once I’d worked out what the rules of the whole thing were (that there really weren’t any rules). I sometimes thought it should bother me more, that it didn’t bother me that my boyfriend wore women’s clothes. But there was no feeling of discomfort if Gabriel showed up in trousers or a dress, wearing makeup or without.

I had eventually pieced together enough to realise that Gabriel didn’t actually identify with either gender, not on any level that counted, he said things like “Biologically male” and “gay” mostly because other people needed labels. To me he had become just Gabriel, and I was happy enough to just let that roll for now. And I can only hope nothing will ever change that.

Dean made it a point to ask if I was having sex every time he spoke to me, not out of some real desire to know the details, but to assure himself, in his own maddening way that I was happy. I’d never understood his preoccupation with sex, or how it equated directly with happiness, but I’d drop in some comments I knew would make him cringe and hadn’t yet been disappointed.

As for myself and Gabriel, we’d been dating nearly six weeks, when Gabriel, curled up on my bed, wearing one of my t-shirts, tapping away on his iPad said causally.

“My uncles want to meet you.”

I stilled, pen stopped dead in the middle of a word in the notes I had been, up until then, copying diligently. How long had I gone before I’d officially met Jessica’s parents? Had it been different because we’d been so young?

“You don’t have to.” Gabriel told me, his tone making it very clear that he meant it. Gabriel was never bothered no matter what my decisions were.

I’d been learning a little about his uncles. Mostly generic things, like how his Uncle Balthazar was a small time actor in pantomimes and local plays and was a bit of flighty sort. He was, Gabriel had snorted, the most stereotypical gay man in their local area, in public at least. His Uncle Crowley was a businessman, who owned and ran no less than three separate businesses’, he also managed Balthazar’s little theatre troop.

Gabriel worked every Saturday in the café/bookshop his uncle owned as a way to feel less guilty over the way Crowley would just hand over any money he needed. 

When he wasn’t managing his impressive collection of shops and cafés and whatever else he was into, Uncle Crowley managed the household and the lives of all those within. I thoughts it all sounded very controlling, and had blurted it out once. Gabriel had just laughed and told me that it wasn’t done to control; it was done because it was the only way Crowley knew how to show love.

All in all, with what I knew about his Uncles, I wasn’t sure how exactly I felt about meeting them.

“Seriously,” Gabriel said, breaking into my musings. “I don’t mind telling them to piss off if you don’t want to. Balthazar is a nosy bastard anyway.”  
I considered the option momentarily, before discarding it, because I knew Gabriel wanted to introduce me to them, no matter what he said. “No, that’s ok. When?”

I caught Gabriel’s surprised expression out of the corner of my eye, which melted quickly into his usual smile by the time I’d turned fully to face him. “Cool. Sunday ok?”

I smiled back. “Sure.”

~*~

Gabriel never stayed over on Saturday. He did his shift at his uncle’s café and spent the night with his uncles. So on Saturday morning, after he’d wriggled back into his blue skirt and swapped my t-shirt for his own; Gabriel leant across to kiss me, where I was sprawled, unwilling to get up so early.

“See you Sunday Sam. I left directions on your desk.”

I didn’t start getting nervous about the whole thing until that evening. I had to stop myself from texting Gabriel a hundred times through what I knew was a marathon of British crime dramas on Netflix. I didn’t know what exactly I intended to text him about, but to save myself any embarrassment, because I knew my boyfriend and I knew the teasing that would follow, I called Dean instead.

Which wasn’t the best alternative, but was at least an alternative.

“Hey Sammy!” Dean answered on the fourth ring cheerfully, which meant he was out drinking.

“Hey Dean.” I said, fumbling for a second as it finally hit me how much of an idiot I was going to see, calling my big brother about this. But before I could come up with an excuse to hang up the noise I could hear in the background dropped as Dean moved somewhere quieter.

“What’s up Sammy?”

“Uh… nothing really.” I said.

Dean snorted, disbelieving, like I knew he would, because I sucked at lying to my brother. “Don’t like to me little brother. You get dumped?”

“What?” I wasn’t sure how Dean had reached that conclusion. “No! No, me and Gabriel are fine.”

“So why are you calling me on a Saturday night dude?” Dean asked, as if that explained everything.

I didn’t even want to grace that with an answer, so instead I carefully considered how I was going to tell Dean what my problem was without sounding completely idiotic. “I’m meeting his uncles tomorrow. For dinner.”

I’d told Dean a little about Gabriel’s Uncles of course, and Dean had rallied back with all manner of questions that I’d been scandalised at. All of which revolved around Gabriel’s parents and why he wasn’t still living with them. Gabriel would tell me when he was ready, and I wasn’t about to bring it up, not when I was keeping my own secrets.

“Ok.” Dean said, slowly and carefully. “And what? You worried about it or something?”

“Or something.” I muttered, rolling my eyes.

Dean sighed. “Why? I mean, I thought you liked the guy.”

“I do.” I said.

“So don’t worry about it. If his uncles are douchebags then screw’em.”

“No helping Dean.” I sighed.

Dean gave a short laugh. “So don’t call me for stupid shit Sammy.”

There was some idle chat about Dad and Cassie, and Cas and Amelia, because Dean and Cas were too terrifyingly close for either of them not to know absolutely everything about each other’s lives. I felt a little sorry for Cassie and Amelia and wondered if they knew how much of their relationships were shared with someone else.

By the end of it I was feeling better. 

I didn’t need to worry.


	8. Dinner with the Uncles

My newfound confidence lasted right up until I was standing outside Gabriel’s house, hands sweating around the wine bag. Which contained the least expensive of the three wines Gabriel had listed for me when I asked what his uncles drink of choice was.

It was the cheapest because the other two were so far outside my budget it made me feel like a scrounging student (which, oh look, I was!).

I rang the doorbell and waited nervously. The man who answered was tall, not as tall as me, but then few people are. He was wearing a low necked shirt and eyeing my critically. I shifted a little under that piercing stare and wondered if this might be Crowley.

“Is that Sam?” came Gabriel’s voice from deeper in the house.

The man didn’t answer immediately, raking over him once. “Does Sam look like a lost puppy on steroids?”

Gabriel’s laugh was loud and happy and he appeared in the hall. “Yeah Balthazar, that’s him.”

The man’s protective stance, which I only recognised for what it was then, relaxed and he smirked. “In you get then darling.” He waved me inside with a flourish. “I’ll go rouse Crowley out of the kitchen. Don’t spend to long out here, you know how he gets.”

Balthazar slipped past Gabriel and disappeared down the hall and all of a sudden Gabriel was crowding up to me. “Sm, you need to stop looking so nervous!” there was a definite smirk on his face. “Balthazar is going to eat you alive!” then Gabriel was on his tiptoes to hook his arms comfortably around my neck, and I let him pull me down for a kiss. “Ready for this?” he asked as he pulled away.

“God no!” I breathed.

Gabriel smirked again, wicked and pleased. “Buck up Sammy-boy.” He said cheerfully. “You haven’t even met Uncle Crowley yet!”

If Balthazar was nerve wracking on his own, and entirely not what I had expected, I will fully amidst I was almost afraid to follow Gabriel in to meet Crowley. But he laced his fingers through mine and I let him tug me down the hallway.

Gabriel was bare footed, I noticed, under a gypsy skirt that hung to his ankles, a plain white top and a cross between a shawl and a brightly coloured jacket was wrapped around his shoulders. Without makeup, which he had forgone tonight, it should have looked ridiculous, he should have looked like a man in drag, because he was broad shouldered and masculine featured, but he didn’t, he could easily pass for a woman, tomboyish yes, but nothing anyone would think twice about.

I pulled back on our joined hands, making him stop. He turned to me in confusion. “You look beautiful.” I told him, in complete sincerity.

His face softened, just a little, before he pulled me the last few steps into the dining room.

Uncle Crowley wasn’t quite how I had pictured him. He was shorted than Balthazar, and was dressed in a sharp suit. Gabriel had warned me about that, had assured me that I was not to feel underdressed; it was just how Uncle Crowley was. He was imposing in his own way, but seemed a lot less of the obsessive control freak Gabriel’s stories made him out to be.

~*~

Dinner passed easily enough once I managed to stop blushing at all of Balthazar’s innuendos. It was easy to see where all of Gabriel’s confidence came from. With an uncle as open and confident as Balthazar there really wasn’t any place for shame. Which made me glad.

“Why do you only call Crowley uncle?” I asked at last, as the main course wound down, and my curiosity refused to be stamped down anymore.

“Because they’re both bloody buggers!” Crowley scowled, but there was no real heat in the glare cast of the unrepentant Balthazar and Gabriel.

Gabriel gave me a wink and whispered, sotto voiced and easily heard. “It’s because he hates it.”

“Too bloody right I do.” Crowley said. “Go and get desert brat.”

Gabriel grinned, flashed me a thumbs up and vanished from the dining room, leaving me to face the uncles alone. It had probably been arranged from the very start.

“Gabriel tells us you’re studying law.” Crowley began.

I nodded. “Yeah, I’m hoping to go into criminal law.”

“Interesting choice.” Crowley said, leaning forward and resting his elbows on the table, watching me carefully.

“How long have you been gay?” Balthazar interrupted, startling me and making Crowley sigh. “What? It’s a valid question!”

Crowley sighed again, shaking his head. “You’re supposed to lead up to it darling.”

Balthazar shrugged, unrepentant, focusing his fully attention on me. “Well?”

I found myself rendered momentarily speechless, and did my best to rally. “I… I’m Bi!” I said at last, my eyes dropping away. “I guess.” Because it was true, I must be.

“You guess?” Balthazar pushed, and there was an edge of something to his voice.

Crowley sighed again. “What Balthazar is trying to determine is whether you are dating Gabriel because he dresses like a woman, or if the fact that he does is going to embarrass you further down the line. Is he a convenient way to pretend that you’re still straight in public, while catering to your urges for men in private?”

“Uh… neither?” it came out as more of a question, and I berated myself, here I was training to become a lawyer and I was babbling like a poorly coached witness. The uncles, when I glanced up at them, were giving me identical disbelieving looks and I had to explain. “Gabriel is… well… Gabriel.” Was the best I could come up with, but I held Crowley’s gaze, somehow knowing he’d be the one I’d have to convince.

Finally, after a long silence, where I felt a little like Crowley was reading me right down to my very soul, he nodded. Balthazar relaxed then, though he still eyed me suspiciously for an extra few seconds.

“Talking about me I hope!” Gabriel grinned, pushing his way back into the room, loaded with a tray of desert.

“Reign in the ego brat. You don’t want to turn out like Balthazar do you?” Crowley snarked out.

Balthazar reached across and swatted Crowley’s arm lightly. Gabriel laughed, and I felt like I had passed some kind of a test, and desert was a whole lot easier conversation wise.

~*~

I was shooed upstairs two hours and four glasses to very expensive wine later, followed by colourful innuendos from Balthazar that left me blushing all over again and stuttering excuses to walk back to my dorm. Crowley’s response to that was to put his foot down with; “I’m going that way tomorrow anyway to leave the brat in for his 9 o’clock class. Do you have to start earlier?”

“No sir.” Was my only response, because apparently I sucked at lying to people other than my brother as well, and it was decided that I’d be staying the night.

Gabriel did his best to keep a supportive, understanding expression in place, but I could very clearly see the amusement in his honeyed eyes.

“I told you not to look so nervous.” He told me cheerfully, pushing me ahead of him up the stairs and into the room directly to the left when we reached the top. I wanted to say ‘You try not being nervous’ but it would sound petty, and Gabriel would just laugh at me anyway.

Gabriel’s room wasn’t anything like the rest of the house, which was decorated in reds, gold’s and greens. Not in the tacky Christmas way, but refined and comfortable. Crowley had apparently chosen the decor, simply because, he’d explained, they’d be sitting on some horribly uncomfortable modern art pieces that Balthazar would buy on a whim because they looked good and would then complain about bitterly for months after.

Crowley had been only too glad when they had moved to America from England because they’d had to leave all the furniture behind them.

Gabriel’s room, by comparison looked like the dream room of every teenage girl, well, sort of, what with the sports posters and action movie posters adorning the walls alongside famous actors… and some rather odd articles from tabloids about crocodiles eating college professors, and slow dancing with aliens.

It made me want to revise Gabriel’s age, despite having seen his learners driving license. It was hard enough before seeing his room to believe that Gabriel was 26, a whole 4 years older than me.

“Needs a bit of redecoration.” Gabriel said suddenly, and a quick glance confirmed that I was not hearing things and he was actually embarrassed.

“It’s fine.” I reassured, my mind flashing back to my own bedroom that still looked like a fifteen year old lived in it. I made a note to have Cas do something about it before the summer, because asking Dean to make it look less teenage would not make things better.

“Yeah, well, at least I have a double bed.” He pointed out, and from the way he complained that he had no room to stretch on my little dorm bed, that was a huge step up for him.

It took me a few seconds too long to realise that his triumphant smirk had turned suggestive and I help up my hands to ward him off. “No! no, no, no, no, no!” I said as firmly as I could. “We are not having sex.”

Gabriel pouted. “Why?”

I looked wildly at the door, which was still standing open, half expecting to find Balthazar and Crowley standing there watching. “Your uncles are in the house!” I hissed.

Gabriel outright laughed at that. “They won’t care! In fact, Balthazar will be disappointed if we don’t.” I groaned at the very thought of that. Gabriel took my hands and smiled. “He’ll tease you about it in the morning whether we did it or not.”

I pulled away. The idea of having sex, even as limited as it was between us, with his guardians in the house. It was like when I’d first started getting ‘morning wood’ and had to deal with it knowing my dad and brother were in the house, and might be able to hear me. It was embarrassing on so many different levels.

“Hey.” Gabriel tried again, softer this time. “He doesn’t mean anything by it. Not in a nasty way. It’s just the way he is. He likes you or he wouldn’t do it at all.”

It took me a moment to realise that Gabriel was becoming genuinely concerned by my reaction, and I forced myself to calm down, to think about it from outside my own crippling embarrassment. “Sorry.” I said at last. “I just get-“

“Nervous?” Gabriel smiled. “I get that. The two of them freaked me right out when I first started living with them.”

“Yeah?” I asked, sensing Gabriel might just reveal something about himself and his life before 17.

Gabriel shrugged. “Yeah, my family were never big on self-expression. So Balthazar and Uncle Crowley were a shock to me when I met them. But it’s just the way they are.”

I rubbed my hand over my face before I stepped forward, leaning down to kiss him. “I’m sorry, I’m being an ass.” I said, because I was. Dean was always telling me I needed to stop being so uptight, and I was lucky that Gabriel was so easy going and laidback enough to not be too bothered by my reactions.

Gabriel kissed me back. “So no sex?”

“If that’s ok?”

Gabriel shrugged. “I’ll let you off this time, but they don’t go out too often unless Balthazar is directing a play, so you had better get over it.”

“I’ll work on that.” I agreed, but cringed at the idea of doing anything more than kissing with what amounted to Gabriel’s parents in the house.

Gabriel shut the door and wriggled out of his skirt and top, waving at me to do the same, tossing a t-shirt at me that I recognised as one of mine that I thought had gone missing in the last wash. I didn’t say anything, because it was sort of cute that he wore my clothes, and it didn’t feel weird that he’d somehow managed to end up taking some home with him. I had some of his tucked away in only of my drawers that he had left behind on morning’s he’d been in a rush.

I couldn’t help but wonder, sometimes, if this was moving a little too fast. But then Gabriel would give me his contented smile, curl up against me, as close as he could get despite his complaints about not being able to sprawl, and I’d sort of forget to wonder about it.

I tried not to think about how that was probably going to come back and bite me at some point.

**Notes for the Chapter:**

> I feel the need to note that there has been no penetrative sex between Sam and Gabriel, because not all couples feel comfortable going that far, not at first anyway (or sometimes at all). And there are lots of different ways to have sex without penetration.
> 
> Another note I'd like to make (Which I maybe should have done in an earlier chapter) is that Gabriel is genderfluid, in the sense that he slips from one gender to the other, and sometimes feels like neither. He wears womens clothes because he likes them and they're comfortable for him, he wears mens clothes more often when he's nervous and needing added protection emotionlly (when he feels he might need to protect himself, a direct throwback to his family life before 17, when he had to conform to what a boy should be). I refer to him as a 'him', for simplicities sake, like he choses to label himself as biologically male and gay, because it's easier than trying to explain to someone else that none of those things really apply, excet when he feels male or female or whatever.
> 
> At any rate, thank you all so much for the kudos and I hope you continue to enjoy the story.


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